Phase equilibrium in binary systems of ionic liquids, or deep eutectic solvents with 2-phenylethanol (PEA), or water

Urszula Domańska-Żelazna , Okuniewska Patrycja , Anastazja Markowska


The production of 2-phenylethanol (PEA), an important flavor and fragrance compound, with a rose-like odor has been significantly increased last decade. The aim of this study was to propose a new ionic liquids (ILs) and Deep Eutectic Solvents (DES) as an entrainers in a biphasic systems in possible bioproduction of PEA. ILs and DESs reveal many unique properties which make them very interesting for applications in modern ‘green’ technologies. In present contribution we have reported new experimental results on (solid, or liquid + liquid) phase equilibrium (SLE/LLE) measurements of eight binary systems composed of pyrrolidinium-based, imidazolium-based and phosphonium-based ILs (namely: 1-butyl-1-methylpyrrolidinium tricyanomethanide, [BMPYR][TCM], 1-butyl-1-methylpyrrolidinium tetracyanoborate, [BMPYR][TCB], 1-butyl-1-methylpyrrolidinium trifluoromethanesulfonate (triflate), [BMPYR][CF3SO3], 1-butyl-1-methylpyrrolidinium tris(pentafluoroethyl)trifluorophosphate, [BMPYR][FAP], and 1-butyl-1-methylpyrrolidinium dicyanamid, [BMPYR][DCA], 1-butyl-1-methylimidazolium tricyanomethanide, [BMIM][TCM] and trihexyl-tetradecyl-phosphonium tricyanomethanide, [P6,6,6,14][TCM] with PEA and water. The complete miscibility with PEA was observed for [BMPYR][FAP], [BMPYR][DCA] and [BMIM][TCM]. The best solubility of solid IL in PEA was found for [BMPYR][TCM]. Complete miscibility with water was observed for [BMPYR][CF3SO3] and [BMPYR][DCA]. Moreover, new results on SLE/LLE of six binary systems of DES: {choline chloride + resorcinol (1:4), or phenylacetic acid (1:1), or phenylacetic acid (1:2), or oxalic acid (1:1), or malonic acid (1:1)} and {acetylocholine chloride + 1,10-decanediol} are shown. The initial information of the eutectic temperature and composition was found for {acetylocholine chloride + 1,10-decanediol}. Complete miscibility with PEA was observed only for {choline chloride + malonic acid (1:1)}. Simple eutectic systems of phase behavior with complete miscibility in the liquid phase for all the later mixtures were observed. The solubility of DES in water reveals SLE/LLE phase equilibrium. The best solvent was {choline chloride + malonic acid (1:1)}. The modeling of liquidus curves of ILs in PEA was proposed with excess Gibbs energy model, NRTL. It correlates the solubility with the average root mean square deviation, σT = 0.78 K. To our best knowledge this is the very first paper when the SLE/LLE of PEA and water have been tested for systems with ILs and DESs.
Author Urszula Domańska-Żelazna ZChF
Urszula Domańska-Żelazna,,
- Department Of Physical Chemistry
, Okuniewska Patrycja ZChF
Okuniewska Patrycja,,
- Department Of Physical Chemistry
, Anastazja Markowska ZChF
Anastazja Markowska,,
- Department Of Physical Chemistry
Journal seriesFluid Phase Equilibria, ISSN 0378-3812
Issue year2016
Nosp. issue
Publication size in sheets0.5
Keywords in EnglishIonic liquids; DES; PEA; Binary (solid or liquid+liquid) phase equilibrium; Correlation
Languageen angielski
1-s2.0-S0378381215301734-main.pdf (file archived - login or check accessibility on faculty) 1-s2.0-S0378381215301734-main.pdf 983.48 KB
Score (nominal)30
ScoreMinisterial score = 30.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2016 = 2.473 (2) - 2016=2.499 (5)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.